A combination of earlier magazine work and new blog posts

What Price Hip?

John Leland knows hip. The 45-year-old New York City native has had his journalist’s eye on the center of modern hip since the mid 1980s. That was when he was writing travel brochures for a tour operator, and heard about the launch of a new music magazine, Spin. An avid music fan, Leland sent an unsolicited letter proposing that Spin let him write a column on 12-inch singles, which then ruled the music biz (he has a personal collection of several thousand). The mag’s founder, Bob Guccione, Jr., son of Penthouse’s owner, liked the idea. Leland carved out a niche at Spin. His smart opinions and writing earned him an enormous following of fans who flipped immediately to his column and to learn about key new bands, performers and releases. By the time he left Spin in 1989, he was the music editor. Now a reporter at The New York Times, he has had stints along the way as editor in chief of Details, and also the editor of Newsweek’s Lifestyle section. But anyone who had any doubts that Leland is an expert in hip will become a believer if they pick up his thoroughly entertaining and critically acclaimed book, Hip: The History (Ecco, 526.95).

In Miami for the Book Fair in November, he sat down with us at South Beach’s Big Pink café for a talk about his book, life and career. What is most striking about Leland on first meeting him is that he isn’t at all the snobby arbiter of style and cool that one might expect from his stature on the subject. Yes, he might sport an obligatory royale (a tuft of hair under the lip), but he is utterly approachable and without pretense.

“It’s the question I am asked most often,” he says, flashing a smile that seems as natural to him as a scowl does to George Bush. “No, I’m not hip. And I don’t want to be the Miss Manners of hip.” Dressed in open-toe sandals, simple pants and an old T-shirt, all of which would be a fashion bar from Mynt, Leland didn’t play at being cool by toying with sushi-grade tuna and Vox vodka, but instead went straight for the BLT, chased down with plain water and then some black coffee. There were no cigarettes. No role-playing.

“When my agent came up with the idea for the book,” he says, “I was wary of it. I actually thought it would be a book about the cool kids in the school cafeteria written by the guy who never got to sit with them. But the more I thought about it, the more I realized it dealt with the questions I had been asking in my journalism for 20 years.”

Leland did not want to make it “an arrogant book.” He succeeded. Hip manages to be the most comprehensive and accessible history of the word in print. Leland’s research is thorough. He seems to have listened to all the music, read all the books, watched all the movies. And he writes with the confidence of someone in absolute control of his material. Eschewing sound bites, Leland instead offers up a serious blend of sociology and history that might surprise some readers attracted initially by the strikingly contemporary cover (very hip).

“My biggest surprise in doing the book was how far back all these things go,” he says. Leland isn’t kidding. ‘The word goes back to the 1700s. It was brought to America by slaves and came from the African Wolof tribe. ‘Hipi’ is ‘to open one’s eyes,’ and ‘hepi’ means ‘to see.’ During the 1910s and 1920s, the commercialism about hip was just as prevalent as it is today, and there was just as much discussion about the youth culture in 1913 as there was in 1993.”

Leland covers the usual trappings of the Lost Generation and the Harlem Renaissance, but he pushes into uncharted territory with his analysis that hip is very much the story of American race relations. Blacks and whites have liberally borrowed, interpreted and assimilated everything from music to language from each other. According to Leland, hip is simply the result of European immigrants and African slaves building a new nation, the process of inventing themselves as Americans.

“Purism is boring,” he says. “I prefer the hybrids that fill our lives, when people on one side borrow from people on the other.” A perfect example is what he calls the “white boy who stole the blues,” a consistent thread that runs from Mark Twain to Elvis to Eminem.

“It’s not symmetric, but both whites and blacks need each other. You can’t get to Myles Davis without white sources. You can’t get to black English without white English.”

The people who make hip often operate on the edges of society: outlaws, gangstas, dope addicts, dropouts, gays and lesbians. From Harlem’s jazz musicians to Greenwich Village’s beatniks to youth cultures such as punk, graffiti art and hip-hop, hip is never conventional.

“There’s a restlessness to really hip people,” he says. “They aren’t mainstream. And they often are deeply flawed, as with Miles Davis, Jack Kerouac and many others. Sometimes, they are less likable once you know more about who they were.”

There is an entire chapter on drugs and the role they have played in hip, with a long roster of hipsters who self-destructed through dope, mostly heroin. “What dope offers,” Leland writes, “is a suspension of responsibility, a fuckup’s version of grace.” But he is also convinced that “nothing is hip about taking drugs to be hip.” Hip, as Leland is quick to point out, can rationalize “poor choices in life. It can squander money, love, talent, even lives.”

But while the truly hip might often be those marginalized in society, Leland is convinced hip would die if it were only stuck with them. The media is needed to broadcast to the wannabes what is hip and fashionable. Today the Internet compresses the time it takes people in remote towns to find out what is hot in inner cities thousands of miles away. And large corporations have packaged and sold hip to an entire generation that thinks it’s possible to buy it from a store shelf.

That doesn’t bother Leland as much as one might expect, because he thinks it’s just part of what companies in a capitalist society do-try to find ways to make people want their products-and few things work better than selling cool. “But real hip,” says Leland, “is much more than what you wear or drive or where you live. It is also a form of enlightenment.”

But more than anything else, Leland has come to understand that “hip is always subjective.” It’s why a good crowd of people at a dinner party can debate all night whether Run-DMC, Jay-Z, Chuck D., Tupac Shakur or Eminem is the real deal.

Hip is a wonderfully entertaining look into a cultural concept as hard to pin down as it is compelling. But Leland is certain that South Beach fits the definition of the word to which he has devoted an entire book. “Absolutely,” he says with a big smile. “South Beach is the theme park of hip.”